Sodium Carbonate → HCID 86613790, compound

HRID 2378108Notes

Reaction equation

HRID 2378108 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([NH:19]C(=O)C)[CH2:9][C@@H:8]1[CH2:23][CH3:24])=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+]>Cl>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([NH2:19])[CH2:9][C@@H:8]1[CH2:23][CH3:24])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86760798HCID 86760798, compound

Product 1

HCID 86613790HCID 86613790, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Heat at 80° C. a solution of (+/−)-cis-4-acetylamino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (100 mg, 0.298 mmol) in 5 N HCl (1 mL) for 4 h. Cool the reaction mixture to room temperature, pour the crude onto a saturated solution of sodium carbonate and extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure, to afford the title compound (85 mg, 98%). MS (ES+): 277 (M−NH2).

Workup

  1. extractionextract with dichloromethane
  2. dry with materialDry the organic layer over anhydrous sodium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-29b0895880124e0099dee9b25d35f746
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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